CA2584411A1 - Compositions pharmaceutiques dotees d'une activite coupe-faim - Google Patents
Compositions pharmaceutiques dotees d'une activite coupe-faim Download PDFInfo
- Publication number
- CA2584411A1 CA2584411A1 CA002584411A CA2584411A CA2584411A1 CA 2584411 A1 CA2584411 A1 CA 2584411A1 CA 002584411 A CA002584411 A CA 002584411A CA 2584411 A CA2584411 A CA 2584411A CA 2584411 A1 CA2584411 A1 CA 2584411A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- extract
- formula
- hoodia
- plant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000002830 appetite depressant Substances 0.000 title claims abstract description 113
- 230000000694 effects Effects 0.000 title claims abstract description 102
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 258
- 238000000034 method Methods 0.000 claims abstract description 149
- 241001504226 Hoodia Species 0.000 claims abstract description 121
- 239000000284 extract Substances 0.000 claims abstract description 119
- 241000196324 Embryophyta Species 0.000 claims abstract description 91
- 230000008569 process Effects 0.000 claims abstract description 79
- 235000017277 hoodia Nutrition 0.000 claims abstract description 70
- 239000003814 drug Substances 0.000 claims abstract description 29
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 claims abstract description 21
- 241001465754 Metazoa Species 0.000 claims description 147
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 113
- 239000000203 mixture Substances 0.000 claims description 100
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 98
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 93
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 83
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 62
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 54
- 239000000463 material Substances 0.000 claims description 51
- 239000002904 solvent Substances 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- -1 monosaccharide compound Chemical class 0.000 claims description 43
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 38
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 36
- 150000001720 carbohydrates Chemical class 0.000 claims description 36
- 235000014633 carbohydrates Nutrition 0.000 claims description 36
- 150000003431 steroids Chemical class 0.000 claims description 33
- 125000005607 tigloyl group Chemical group 0.000 claims description 28
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 27
- 235000019789 appetite Nutrition 0.000 claims description 24
- 230000036528 appetite Effects 0.000 claims description 24
- 238000000605 extraction Methods 0.000 claims description 24
- 150000002895 organic esters Chemical group 0.000 claims description 24
- 241001504224 Hoodia gordonii Species 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 208000008589 Obesity Diseases 0.000 claims description 21
- 230000008878 coupling Effects 0.000 claims description 21
- 238000010168 coupling process Methods 0.000 claims description 21
- 238000005859 coupling reaction Methods 0.000 claims description 21
- 235000020824 obesity Nutrition 0.000 claims description 21
- 239000000843 powder Substances 0.000 claims description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 19
- 239000008103 glucose Substances 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 150000004043 trisaccharides Chemical class 0.000 claims description 16
- GOYBREOSJSERKM-DSYKOEDSSA-N D-cymarose Chemical compound O=CC[C@H](OC)[C@H](O)[C@@H](C)O GOYBREOSJSERKM-DSYKOEDSSA-N 0.000 claims description 15
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 15
- 238000013375 chromatographic separation Methods 0.000 claims description 15
- 229930002534 steroid glycoside Natural products 0.000 claims description 14
- 150000008143 steroidal glycosides Chemical class 0.000 claims description 14
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- 108010021436 Type 4 Melanocortin Receptor Proteins 0.000 claims description 11
- 239000002552 dosage form Substances 0.000 claims description 11
- 239000003937 drug carrier Substances 0.000 claims description 11
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 11
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 10
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 239000000018 receptor agonist Substances 0.000 claims description 9
- 229940044601 receptor agonist Drugs 0.000 claims description 9
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- MPQBLCRFUYGBHE-XZBKPIIZSA-N (2r,3s,4r,5r)-2,4,5-trihydroxy-3-methoxyhexanal Chemical class O=C[C@H](O)[C@@H](OC)[C@H](O)[C@@H](C)O MPQBLCRFUYGBHE-XZBKPIIZSA-N 0.000 claims description 7
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 claims description 7
- 238000003825 pressing Methods 0.000 claims description 7
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 claims description 7
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 6
- 235000013361 beverage Nutrition 0.000 claims description 6
- 150000002772 monosaccharides Chemical class 0.000 claims description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 6
- 235000011150 stannous chloride Nutrition 0.000 claims description 6
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims description 6
- GOYBREOSJSERKM-UHFFFAOYSA-N D-oleandrose Natural products O=CCC(OC)C(O)C(C)O GOYBREOSJSERKM-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000000638 solvent extraction Methods 0.000 claims description 5
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 239000000556 agonist Substances 0.000 claims description 4
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 claims description 4
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 4
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims description 3
- UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 claims description 3
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 claims description 3
- 150000002016 disaccharides Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 claims description 3
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 claims description 3
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 claims description 3
- UYUXSRADSPPKRZ-UHFFFAOYSA-N 2-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxyacetaldehyde Chemical group O=CC(O)C1OC(=O)C(O)C1O UYUXSRADSPPKRZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- VJMQFIRIMMSSRW-UHFFFAOYSA-N trimethyl(phenylsulfanyl)silane Chemical compound C[Si](C)(C)SC1=CC=CC=C1 VJMQFIRIMMSSRW-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 8
- 102000001796 Melanocortin 4 receptors Human genes 0.000 claims 6
- 238000002560 therapeutic procedure Methods 0.000 claims 5
- 229940126214 compound 3 Drugs 0.000 claims 4
- 239000007868 Raney catalyst Substances 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 21
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- 238000003786 synthesis reaction Methods 0.000 abstract description 8
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 54
- 239000000243 solution Substances 0.000 description 49
- 238000012360 testing method Methods 0.000 description 49
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
- 235000012631 food intake Nutrition 0.000 description 30
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 30
- 239000003981 vehicle Substances 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 29
- 239000010410 layer Substances 0.000 description 28
- 235000019341 magnesium sulphate Nutrition 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 241000700159 Rattus Species 0.000 description 24
- 229940093499 ethyl acetate Drugs 0.000 description 24
- 235000019439 ethyl acetate Nutrition 0.000 description 24
- 210000004185 liver Anatomy 0.000 description 23
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 230000001965 increasing effect Effects 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- 235000013305 food Nutrition 0.000 description 17
- 230000009467 reduction Effects 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 101150041968 CDC13 gene Proteins 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 230000037396 body weight Effects 0.000 description 14
- 238000010898 silica gel chromatography Methods 0.000 description 14
- 230000003247 decreasing effect Effects 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 12
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 11
- FCYQTGCEDUOHLT-LEKSSAKUSA-N 1-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 FCYQTGCEDUOHLT-LEKSSAKUSA-N 0.000 description 11
- 229960001582 fenfluramine Drugs 0.000 description 11
- 229960003387 progesterone Drugs 0.000 description 11
- 239000000186 progesterone Substances 0.000 description 11
- 239000008213 purified water Substances 0.000 description 11
- 241000463291 Elga Species 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 230000037406 food intake Effects 0.000 description 10
- 230000007170 pathology Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 230000008961 swelling Effects 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 206010061998 Hepatic lesion Diseases 0.000 description 9
- 230000008859 change Effects 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000012280 lithium aluminium hydride Substances 0.000 description 9
- 231100000161 signs of toxicity Toxicity 0.000 description 9
- 101150032984 DHS1 gene Proteins 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- 101100435897 Petunia hybrida DAHP1 gene Proteins 0.000 description 8
- 101100333991 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) EXO1 gene Proteins 0.000 description 8
- 238000004166 bioassay Methods 0.000 description 8
- 101150021184 fhs1 gene Proteins 0.000 description 8
- 210000003494 hepatocyte Anatomy 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 150000008188 altrosides Chemical class 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 238000011886 postmortem examination Methods 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- SHZGCJCMOBCMKK-GASJEMHNSA-N (3r,4s,5s,6r)-6-methyloxane-2,3,4,5-tetrol Chemical compound C[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O SHZGCJCMOBCMKK-GASJEMHNSA-N 0.000 description 5
- FKEAXDOASBXJKP-SPGTZJEESA-N (8R,9S,10R,13S,17R)-3',10,13-trimethylspiro[1,2,7,8,9,11,12,16-octahydrocyclopenta[a]phenanthrene-17,2'-1,4-dioxane] Chemical compound C1OC(C)[C@]2(CC=C3[C@@H]4CC=C5C=CCC[C@]5(C)[C@H]4CC[C@]23C)OC1 FKEAXDOASBXJKP-SPGTZJEESA-N 0.000 description 5
- 208000031638 Body Weight Diseases 0.000 description 5
- 102000008316 Type 4 Melanocortin Receptor Human genes 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 5
- 238000007385 chemical modification Methods 0.000 description 5
- 230000034994 death Effects 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000401 methanolic extract Substances 0.000 description 5
- 229920001592 potato starch Polymers 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- FOLRUCXBTYDAQK-SFZUHQLGSA-N (4ar,7r,8r,8as)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol Chemical compound C([C@H]1OC([C@@H]([C@@H](O)[C@@H]1O1)O)O)OC1C1=CC=CC=C1 FOLRUCXBTYDAQK-SFZUHQLGSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- PNLYLUYLYDYNFK-LKBIUASMSA-N 5-[(8r,9s,10s,13s,14s,17s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2,3-dihydro-1,4-dioxine Chemical compound C1([C@H]2CC[C@H]3[C@H]4[C@@H]([C@]5(CCCCC5CC4)C)CC[C@@]32C)=COCCO1 PNLYLUYLYDYNFK-LKBIUASMSA-N 0.000 description 4
- 229910010084 LiAlH4 Inorganic materials 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 4
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 150000002338 glycosides Chemical class 0.000 description 4
- 230000006742 locomotor activity Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 239000000419 plant extract Substances 0.000 description 4
- 235000018770 reduced food intake Nutrition 0.000 description 4
- 230000000241 respiratory effect Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
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- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
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- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
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- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
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- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/08—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to sulfur, selenium or tellurium
- C07H5/10—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to sulfur, selenium or tellurium to sulfur
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- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
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- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J17/005—Glycosides
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- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/002—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa not substituted in position 16
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- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/0025—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa substituted in position 16
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/0025—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa substituted in position 16
- C07J7/0035—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa substituted in position 16 by a hydroxy group free esterified or etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/0065—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified
- C07J7/007—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified not substituted in position 17 alfa
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicinal Preparation (AREA)
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ZA97/3201 | 1997-04-15 | ||
ZA973201 | 1997-04-15 | ||
CA002283564A CA2283564C (fr) | 1997-04-15 | 1998-04-15 | Compositions pharmaceutiques dotees d'une activite coupe-faim |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002283564A Division CA2283564C (fr) | 1997-04-15 | 1998-04-15 | Compositions pharmaceutiques dotees d'une activite coupe-faim |
Publications (1)
Publication Number | Publication Date |
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CA2584411A1 true CA2584411A1 (fr) | 1998-10-22 |
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ID=25586362
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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CA002584411A Abandoned CA2584411A1 (fr) | 1997-04-15 | 1998-04-15 | Compositions pharmaceutiques dotees d'une activite coupe-faim |
CA002283564A Expired - Fee Related CA2283564C (fr) | 1997-04-15 | 1998-04-15 | Compositions pharmaceutiques dotees d'une activite coupe-faim |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
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CA002283564A Expired - Fee Related CA2283564C (fr) | 1997-04-15 | 1998-04-15 | Compositions pharmaceutiques dotees d'une activite coupe-faim |
Country Status (40)
Country | Link |
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US (6) | US6376657B1 (fr) |
EP (5) | EP1213020B1 (fr) |
JP (3) | JP3553086B2 (fr) |
KR (2) | KR100891756B1 (fr) |
CN (3) | CN101239089A (fr) |
AP (3) | AP2003002730A0 (fr) |
AT (3) | ATE502041T1 (fr) |
AU (1) | AU746414B2 (fr) |
BG (1) | BG103795A (fr) |
BR (1) | BR9808593A (fr) |
CA (2) | CA2584411A1 (fr) |
DE (3) | DE69840552D1 (fr) |
DK (1) | DK0973534T3 (fr) |
EA (2) | EA002885B1 (fr) |
EE (1) | EE9900497A (fr) |
ES (3) | ES2276460T3 (fr) |
GB (3) | GB2338235B (fr) |
GE (2) | GEP20022788B (fr) |
GT (3) | GT199800076AA (fr) |
HK (1) | HK1026373A1 (fr) |
HU (1) | HUP0000838A3 (fr) |
ID (1) | ID22888A (fr) |
IL (3) | IL158465A0 (fr) |
IS (1) | IS5196A (fr) |
MY (1) | MY141674A (fr) |
NO (1) | NO994992L (fr) |
NZ (5) | NZ516696A (fr) |
OA (1) | OA11166A (fr) |
PE (1) | PE85699A1 (fr) |
PL (3) | PL196015B1 (fr) |
PT (2) | PT1213020E (fr) |
SA (1) | SA98190501B1 (fr) |
SG (1) | SG120054A1 (fr) |
SK (1) | SK141899A3 (fr) |
TR (2) | TR199902540T2 (fr) |
TW (3) | TWI253932B (fr) |
UA (1) | UA72439C2 (fr) |
WO (1) | WO1998046243A2 (fr) |
YU (1) | YU52199A (fr) |
ZA (1) | ZA983170B (fr) |
Families Citing this family (70)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2584411A1 (fr) * | 1997-04-15 | 1998-10-22 | Csir | Compositions pharmaceutiques dotees d'une activite coupe-faim |
CA2381008A1 (fr) * | 1999-08-04 | 2001-02-15 | Millennium Pharmaceuticals, Inc. | Composes fixant les recepteurs de melanocortine-4 et procedes d'utilisation de ces composes |
GB2355657B (en) * | 1999-10-27 | 2004-07-28 | Phytopharm Plc | Inhibitors Of Gastric Acid Secretion |
GB2363985B (en) * | 2000-06-30 | 2004-09-29 | Phytopharm Plc | Extracts,compounds & pharmaceutical compositions having anti-diabetic activity and their use |
KR20040015670A (ko) * | 2001-01-24 | 2004-02-19 | 트리콘 호울딩즈 리미티드 | 탄탈륨 필름 침착방법 |
US7008648B2 (en) | 2001-11-16 | 2006-03-07 | Novartis Nutrition Ag | Plant derived or derivable material with appetite suppressing activity |
US20040265398A1 (en) * | 2002-04-25 | 2004-12-30 | Fleischner Albert M. | Herbal composition for weight control |
US20060233861A1 (en) * | 2003-02-14 | 2006-10-19 | Maclean David B | Modulation of atp production or content in the hypothalamus |
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US7060308B2 (en) * | 2003-06-04 | 2006-06-13 | Ramaswamy Rajendran | Caralluma extract products and processes for making the same |
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- 1998-04-15 ES ES98917372T patent/ES2276460T3/es not_active Expired - Lifetime
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- 1998-04-15 GE GEAP19985030A patent/GEP20022709B/en unknown
- 1998-04-15 EP EP98917372A patent/EP0973534B1/fr not_active Expired - Lifetime
- 1998-04-15 SK SK1418-99A patent/SK141899A3/sk unknown
- 1998-04-15 PT PT98917372T patent/PT973534E/pt unknown
- 1998-04-15 NZ NZ516696A patent/NZ516696A/en unknown
- 1998-04-15 NZ NZ525022A patent/NZ525022A/en unknown
- 1998-04-15 IL IL15846698A patent/IL158466A0/xx unknown
- 1998-04-15 NZ NZ525021A patent/NZ525021A/en unknown
- 1998-04-15 NZ NZ516695A patent/NZ516695A/en unknown
- 1998-04-15 AP APAP/P/1999/001673A patent/AP1291A/en active
- 1998-04-15 ZA ZA9803170A patent/ZA983170B/xx unknown
- 1998-04-15 AT AT98917372T patent/ATE344046T1/de active
- 1998-04-15 DE DE69836321T patent/DE69836321T2/de not_active Expired - Lifetime
- 1998-04-15 CN CNB988041650A patent/CN100378118C/zh not_active Expired - Fee Related
- 1998-04-15 IL IL13165998A patent/IL131659A/xx not_active IP Right Cessation
- 1998-04-15 NZ NZ337422A patent/NZ337422A/en unknown
- 1998-04-15 KR KR10-2003-7005297A patent/KR100510614B1/ko not_active IP Right Cessation
- 1998-04-15 DE DE69842189T patent/DE69842189D1/de not_active Expired - Lifetime
- 1998-04-15 MY MYPI98001667A patent/MY141674A/en unknown
- 1998-04-15 HU HU0000838A patent/HUP0000838A3/hu unknown
- 1998-06-02 TW TW091137164A patent/TWI253932B/zh not_active IP Right Cessation
- 1998-06-02 TW TW087108667A patent/TW539551B/zh active
- 1998-06-02 TW TW091137165A patent/TW589187B/zh not_active IP Right Cessation
- 1998-06-09 GT GT199800076AK patent/GT199800076AA/es unknown
- 1998-06-09 PE PE1998000485A patent/PE85699A1/es not_active Application Discontinuation
- 1998-06-09 GT GT199800076A patent/GT199800076A/es unknown
- 1998-06-09 GT GT199800076BL patent/GT199800076BA/es unknown
- 1998-09-06 SA SA98190501A patent/SA98190501B1/ar unknown
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1999
- 1999-09-24 IS IS5196A patent/IS5196A/is unknown
- 1999-10-08 OA OA9900225A patent/OA11166A/en unknown
- 1999-10-11 BG BG103795A patent/BG103795A/xx unknown
- 1999-10-14 NO NO994992A patent/NO994992L/no not_active Application Discontinuation
-
2000
- 2000-09-14 HK HK00105778A patent/HK1026373A1/xx not_active IP Right Cessation
-
2002
- 2002-01-10 JP JP2002003897A patent/JP2002205997A/ja active Pending
- 2002-02-13 US US10/073,357 patent/US20020168427A1/en not_active Abandoned
- 2002-06-14 US US10/170,750 patent/US20030086984A1/en not_active Abandoned
- 2002-06-25 JP JP2002184593A patent/JP2003026591A/ja active Pending
-
2004
- 2004-06-22 US US10/872,567 patent/US7166611B2/en not_active Expired - Fee Related
- 2004-06-22 US US10/872,463 patent/US20040234634A1/en not_active Abandoned
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2006
- 2006-02-28 US US11/363,057 patent/US20060205931A1/en not_active Abandoned
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